A. Polyester anti-static agents formed from dimethyl terephthalate, ethylene glycol and methoxy PEGs
U.S. Pat. No. 3,416,952 to McIntyre et al., issued Dec. 17, 1968, discloses the treatment of shaped polyester articles with a water-insoluble crystallizable polymeric compound which can contain a water-solvatable polymeric group such as a polyoxyalkylene group having an average molecular weight of from 300-6000. Preferred polyoxyalkylene groups are the PEGs having an average molecular weight of from 1000-4000. Treatment of the shaped articles is carried out by applying an aqueous dispersion of the crystallizable polymeric compound in the presence of an anti-oxidant, followed by heating to a temperature above 90.degree. C. to obtain a durable coating of the compound on the shaped article. Example 6 discloses one such crystallizable polymeric compound formed by the reaction of dimethyl terephthalate, ethylene glycol and an O-methyl poly(oxyethylene) glycol of average molecular weight 350. A 20% solution of this polyester in benzyl alcohol was used to impart anti-static properties to a polyester fabric. Example 7 discloses a 20% aqueous solution of a similar polyester used to impart anti-static properties to a polyester fabric.
B. Polyester anti-static and soil release agents formed from dimethyl terephthalate, sodium dimethyl 5-sulphoisophthalate, ethylene glycol and polyethylene glycol (PEG)
U.S. Pat. No. 4,427,557 to Stockburger, filed Feb. 15, 1983, issued Jan. 24, 1984, discloses low molecular weight copolyesters (M.W. 2,000 to 10,000) which can be used in aqueous dispersions to impart soil release properties to polyester fibers. The copolyesters are formed by the reaction of ethylene glycol, a PEG having an average molecular weight of 200 to 1000, an aromatic dicarboxylic acid (e.g. dimethyl terephthalate), and a sulfonated aromatic dicarboxylic acid (e.g. dimethyl 5-sulfoisophthalate). The PEG can be replaced in part with monoalkylethers of PEG such as the methyl, ethyl and butyl ethers. A dispersion or solution of the copolyester is applied to the textile material and then heat set at elevated temperatures (90.degree. to 150.degree. C.) to impart durable soil release properties.
C. Monomeric polyesters of PEG and terephthalic acid useful as soil release agents
U.S. Pat. No. 4,349,688 to Sandler, issued Sept. 14, 1982, discloses polyoxyalkylene ester soil release agents, in particular monomeric polyesters of PEG and terephthalic acid having the formula: ##STR2## where n can range from 6-23 and X is either methyl or H. Example IV discloses the preparation of one such PEG/terephthalate polyester formed from terephthaloyl chloride and Carbowax 400 (n=9, X=H). Durable soil resistancy and water wicking properties are imparted by wetting the fabric with a composition containing the polyoxyalkylene ester, drying the wetted fabric, and then curing the dried fabric at a temperature of from 190.degree.-200.degree. C. for about 45-90 seconds.
D. Ethylene terephthalate/PEG terephthalate soil release polyesters for fabric treating solutions
U.S. Pat. No. 3,959,230 to Hays, issued May 25, 1976, discloses polyester soil release agents containing random ethylene terephthalate/PEG terephthalate units in a mole ratio of from about 25:75 to about 35:65. These soil release polyesters have a molecular weight of from about 25,000 to about 55,000, (preferably from about 40,000 to about 55,000) and are used in dilute, aqueous solutions, preferably with an emulsifying agent present. Fabrics are immersed in this solution so that the soil release polyester adsorbs onto the fabric surface. The polyester forms a hydrophilic film which remains on the fibers after the fabric is removed from the solution and dried. See also U.S. Pat. No. 3,893,929 to Basadur, issued July 8, 1975 (compositions for imparting soil release finish containing a polyester having an average molecular weight of 3000-5000 formed from terephthalic acid, PEG and ethylene glycol); U.S. Pat. No. 3,712,873 to Zenk, issued Jan. 23, 1973 (textile treating composition comprising fatty alcohol polyethoxylates; quaternary ammonium compounds; a polyester having average molecular weight of 3000-5000 formed from terephthalic acid, PEG and ethylene glycol; and starch).
E. Ethylene terephthalate/PEG terephthalate soil release agents used in detergent compositions
U.S. Pat. No. 3,962,152 to Nicol et al., issued June 8, 1976, discloses detergent compositions containing detergent surfactants and the ethylene terephthalate/PEG terephthalate soil release polyesters disclosed in the Hays patent. See also U.S. Pat. No. 4,116,885 to Derstadt et al., issued Sept. 26, 1978 (detergent compositions containing certain compatible anionic detergent surfactants and ethylene terephthalate/PEG terephthalate soil release polyesters); U.S. Pat. No. 4,132,680 to Nicol, issued Jan. 2, 1979 (detergent compositions containing detergent surfactants; a composition which disassociates to yield quaternary ammonium cations; and an ethylene terephthalate/PEG terephthalate soil release polyester).
F. Soil release and antistatic polyurethanes useful in detergent compositions which contain polyester blocks having sulfoisophthalate units
U.S. Pat. No. 4,201,824 to Violland et al., issued May 6, 1980, discloses hydrophilic polyurethanes having soil release and antistatic properties useful in detergent compositions. These polyurethanes are formed from the reaction product of a base polyester with an isocyanate prepolymer (reaction product of diisocyanate and macrodiol). Example VI discloses a base polyester formed from dimethyl terephthalate, dimethyl sulfoisophthalate, ethylene glycol and PEG (molecular weight 300) which is reacted with a prepolymer formed from a PEG (molecular weight 1,500) and toluene diisocyanate.